The warmth and sun of Florida is an attraction any time of year. Pack your bags and prepare for fun in the sun, water, and even on land as you check out many of the exciting activities the area has to offer. While the weather may be perfect for the majority of your trip, you’ll want to prepare some activities for times when the weather doesn’t cooperate with your beach and outdoor schedule. There are many “rainy day” activities in Siesta Key to enjoy and pass the time when the weather is gloomy.

Browse Our Summer Rentals Here!

Siesta Key Village Shops

Touring a town is a great way to get to know its nooks and crannies as well as the locals. When the sun isn’t shining, that doesn’t mean that the exploration needs to stop, just take it indoors! The charming shops and restaurants found in Siesta Key Village will give you hours of fun, browsing, window shopping, and delicious food to keep your mind off of the pitter-patter of rain outside. You’ll score some great island-themed décor, clothing, and accessories to put on display once you get home and turn your home into an island getaway.

Siesta Key Wine Bar

An activity made especially for the adults of the group is a visit to Siesta Key Wine Bar. The self-billed “home for wine lovers,” the establishment at the north end of Siesta Key Village includes a tasting bar and sitting areas for you to enjoy a glass of terrific wine. The wine bar features local Florida wines, as well as reds, whites, and “bubbles” from across the globe. Visit the wine shop to take home your favorites or arrange to have your favorites shipped to your home. Keep in mind there is limited ability to ship to certain locales and yours may not be available.

Spa Day

While your outdoor relaxation plans may be canceled, that doesn’t mean the relaxation can’t take place indoors. Book yourself some time for rest, relaxation, and rejuvenation at a local spa. Choose from treatments like a mani/pedi, massage, body wrap, facial, and more. Staff will help you create a package just for you so you can fully relax your mind, body, and spirit. Some establishments may offer salon services, so you can get a new cut or style to go with your relaxed mood. Ask about treatments designed especially for the men of the group who need a recharge.

Learn About Summer Activities Here!

Relaxing Rental

You don’t need to go out on the town for a good time, indoors or out, rain or shine. You can always choose to relax around your Rent Siesta Key vacation rental home. Many rentals include books, a movie library, board games, puzzles, and other indoor activities to keep you busy. Staying right where you are can be just as engaging as a day out touring the town. If you have any personal favorite games from home, make sure they make the packing list so you can enjoy those, too, if the mood strikes.


Lift your spirits as the rain falls with a meal out on the town. There are many restaurants on Siesta Key that will satisfy any hunger or thirst you may have. From a casual lunch or dinner to a special date or celebration, you’ll find something delicious to fit the mood.


If the rain insists on lasting another day, or you’ve worn out all the things to do on-island, take a trip to the mainland for some fun. Sarasota is full of fun, with activities like museums, escape rooms, and aquariums, you’ll find something to do to battle the gloom and continue to enjoy your Florida getaway, no matter what the weather is like.

Check Out Our Weekly Rentals Here!

Rainy Day Fun Activities in Siesta Key

When you book your fun-filled getaway to Siesta Key, you won’t be short on activities to fill every minute of every day, even when the sun isn’t shining. With plenty of activities in Siesta Key to choose from, you’ll find something to do to keep the entire group entertained and happy without the sun. Spend some time in your accommodations if you don’t feel like going out. From a one-bedroom for your small family or a getaway with your sweetheart, all the way up to six bedrooms for a family or group reunion with everyone, you’ll find something by Rent Siesta Key to fit your vacation needs and style.

Instead of getting wet when heading out to eat, stay warm and dry and prepare a delicious home-cooked meal in your rental’s fully equipped kitchen. Recharge with a nap or a good night’s sleep in a private bedroom or spread out in the spacious living area to read a book or watch a movie. Indulge yourself in a premium unit for perks and upgrades like stainless steel appliances, double ovens, flat-screen TVs and much more.

Contact us now to book your stay full of all-weather memories!